Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration
Vladimir G Ilkin
1, 2
,
Daan Willocx
2
,
Pavel S Silaichev
1, 3
,
Santhini Pulikkal Veettil
2
,
Wim Dehaen
2
,
Publication type: Journal Article
Publication date: 2022-09-01
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
36049015
Organic Chemistry
Abstract
The reactivity of readily available 4,5-fused-1-sulfonyl-1,2,3-triazoles was examined in the Rh(II)-catalyzed transannulation reaction with nitriles. We have come across the interesting observation that 1-sulfonyl cycloalkeno[d][1,2,3]triazoles that possess β-hydrogens resist intramolecular β-hydride migration and could serve as a new source of Rh-iminocarbenoids for intermolecular Rh(II)-catalyzed transannulation reactions. As a result, 1-sulfonyl cyclohexeno-, cyclohepteno-, dihydropyrano-, 5-phenyltetrahydrobenzo-, and 4,5-dihydronaphtho[d]imidazoles were synthesized from various nitriles in good yields. A one-pot methodology has also been executed for the synthesis of NH-imidazoles.
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8
Total citations:
8
Citations from 2024:
5
(62.5%)
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GOST
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Ilkin V. G. et al. Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration // Journal of Organic Chemistry. 2022. Vol. 87. No. 18. pp. 12274-12286.
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Ilkin V. G., Beryozkina T. V., Willocx D., Silaichev P. S., Veettil S. P., Dehaen W., Bakulev V. A. Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration // Journal of Organic Chemistry. 2022. Vol. 87. No. 18. pp. 12274-12286.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.2c01456
UR - https://doi.org/10.1021/acs.joc.2c01456
TI - Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration
T2 - Journal of Organic Chemistry
AU - Ilkin, Vladimir G
AU - Beryozkina, Tetyana V
AU - Willocx, Daan
AU - Silaichev, Pavel S
AU - Veettil, Santhini Pulikkal
AU - Dehaen, Wim
AU - Bakulev, Vasiliy A.
PY - 2022
DA - 2022/09/01
PB - American Chemical Society (ACS)
SP - 12274-12286
IS - 18
VL - 87
PMID - 36049015
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2022_Ilkin,
author = {Vladimir G Ilkin and Tetyana V Beryozkina and Daan Willocx and Pavel S Silaichev and Santhini Pulikkal Veettil and Wim Dehaen and Vasiliy A. Bakulev},
title = {Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.joc.2c01456},
number = {18},
pages = {12274--12286},
doi = {10.1021/acs.joc.2c01456}
}
Cite this
MLA
Copy
Ilkin, Vladimir G., et al. “Rhodium-Catalyzed Transannulation of 4,5-Fused 1-Sulfonyl-1,2,3-triazoles with Nitriles. The Selective Formation of 1-Sulfonyl-4,5-fused Imidazoles versus Secondary C–H Bond Migration.” Journal of Organic Chemistry, vol. 87, no. 18, Sep. 2022, pp. 12274-12286. https://doi.org/10.1021/acs.joc.2c01456.